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The mol­ecules of the title compound, C10H8O2, are linked by two O—H...O hydrogen bonds, which form infinite chains with a graph-set descriptor of C(6). These chains are linked into puckered (100) sheets of R44(8) and R44(24) rings. Adjacent sheets are connected by weak C—H...π and π–π inter­actions into a continuous three-dimensional network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S010827010504093X/gd1424sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010827010504093X/gd1424Isup2.hkl
Contains datablock I

CCDC reference: 299633

Comment top

In previous papers, we have reported the structures of some mono- and dihydroxynaphthalenes, such as 1-hydroxynaphthalene (1-naphthol; Rozycka-Sokolowska et al., 2004), 2-hydroxynaphthalene (2-naphthol; Marciniak et al., 2003) and 2,7-dihydroxynaphthalene (2,7-naphthalenediol; Rozycka-Sokolowska et al., 2005). Continuing this research, the results of structural studies of 1,3-naphthalenediol, commonly known as naphthoresorcinol, (I) (Fig. 1), are presented here.

The molecule of (I) contains a naphthalene ring and two hydroxyl groups attached to it on atoms C1 and C3. The presence of hydroxyl substituents at positions 1 and 3 modifies the geometric parameters within the aromatic rings. The C—C bond distances (Table 1) vary from 1.354 (3) to 1.410 (2) Å; bonds C1—C2, C3—C4, C6—C7 and C8—C9 are shorter than the typical aromatic bond length of 1.384 (13) Å (Allen et al., 1987), whereas all the other bonds in the aromatic rings are longer. The values of the bond angles within the aromatic rings vary from 117.90 (17) to 121.73 (18)°. Despite these variations in bond lengths and angles, the naphthalene ring remains planar, with an average out-of-plane deviation of 0.006 (2) Å. Atoms O11 and O12 attached to the naphthalene ring deviate from its plane by only −0.034 (1) and 0.033 (1) Å, respectively.

The unit cell of (I) consists of four molecules, which occupy one non-equivalent set of general positions. The molecules are linked together by two strong O11—H11.·O12 (A in Fig. 2) and O12—H12···O11 (B in Fig. 2) hydrogen bonds, forming infinite chains which run parallel to the b and c axes, respectively, and which both have a graph-set motif of C(6) (Bernstein et al., 1995). Together, these hydrogen bonds produce a deeply puckered sheet parallel to (100) containing R44(8) and R44(24) rings, which are arranged alternately in a chessboard fashion (Fig. 2). The non-H atoms belonging to the (100) sheets lie in domains (−0.28 + x) < a < (x + 1.28) (x is zero or an integer). Each sheet is interwoven with two neighbouring sheets and is linked to them by weak C—H···π and ππ interactions to form a continuous three-dimensional network (Fig. 3).

Atom C9 in the molecule at (x, y, z), belonging to the (100) sheet in domain −0.28 < x < 1.28 acts as a hydrogen-bond donor, via atom H9, to the C5–C10 benzene ring (centroid Cg2) of the molecule at (−x, 1/2 + y, 1/2 − z), which belongs to the adjacent sheet lying in domain −1.28 < a < 0.28 (Fig. 3 and Table 2). As mentioned above, in the structure of (I) there are also ππ stacking interactions involving the C1–C5/C10 (centroid Cg1) and C5–C10 (centroid Cg2) rings (Fig. 3). The perpendicular distance of the ring centroids Cg1 and Cg2 from the symmetry-related centroids at (−x, 2 − y, −z), i.e. Cg2iv and Cg1iv, respectively, is 3.42 Å, and the centroid–centroid separation is 3.68 Å. The planes of these rings are practically parallel, making an angle of only 0.6°.

Experimental top

1,3-Naphthalenediol was obtained from Sigma (purity 99%) and used without further purification. Despite many experimental attempts, we were initially unable to grow single crystals suitable for X-ray structure analysis. Among the seven organic solvents (ethanol, methanol, butanol, chloroform, acetone, ethyl acetate and xylene) used in the growth experiments carried out with the help of temperature-lowering and evaporation techniques, only xylene proved suitable for the growth of high-quality crystals of 1,3-dihydroxynaphthalene using the latter method. Only polycrystalline material was obtained when recrystallization was attempted from the other solvents.

Refinement top

H atoms bonded to C atoms were refined in geometrically idealized positions, with C—H distances of 0.93 Å and with Uiso(H) = 1.2Ueq(C). The H atoms of the hydroxyl groups were located in difference maps and refined isotropically, giving O–H distances of 0.85 (3) and 0.89 (3) Å.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2002); cell refinement: CrysAlis RED (Oxford Diffraction, 2002); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003) and RPLUTO (Motherwell et al., 2000); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. A view of the molecule of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii.
[Figure 2] Fig. 2. A unit-cell plot of (I), showing the intermolecular hydrogen bonds in the crystal structure, with the assigned graph-set motifs. Hydrogen bonds are shown as red (motif A) and green (motif B) dashed lines. All C-bound H atoms have been omitted for clarity.
[Figure 3] Fig. 3. Part of the crystal structure of (I), showing the (100) sheets lying in domains −1.28 < a < 0.28 (red), −0.28 < a < 1.28 (blue) and 0.72 < a < 2.28 (violet), as well as the intermolecular O—H···O hydrogen bonds (red and blue dashed lines), C—H···π hydrogen bonds (green dashed lines) and ππ interactions (black dashed lines). [Symmetry codes: (iii) −x, 1/2 + y, 1/2 − z; (iv) −x, 2 − y, −z.] Cg1 and Cg2 are the centroids of the C1–C5/C10 and C5–C10 benzene rings, respectively, and are denoted by small crosses. H atoms, except for atoms H9, H11 and H12, have been omitted for clarity.
Naphthalene-1,3-diol top
Crystal data top
C10H8O2F(000) = 336
Mr = 160.16Dx = 1.414 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3650 reflections
a = 9.0606 (18) Åθ = 4.6–25.0°
b = 7.2027 (14) ŵ = 0.10 mm1
c = 13.309 (3) ÅT = 293 K
β = 119.96 (3)°Plate, red
V = 752.5 (4) Å30.50 × 0.30 × 0.05 mm
Z = 4
Data collection top
Oxford Diffraction Xcalibur3 CCD area-detector
diffractometer
1139 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.025
Graphite monochromatorθmax = 25.0°, θmin = 4.6°
ω scansh = 810
3650 measured reflectionsk = 78
1312 independent reflectionsl = 1514
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.049H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.119 w = 1/[σ2(Fo2) + (0.0492P)2 + 0.1818P]
where P = (Fo2 + 2Fc2)/3
S = 1.17(Δ/σ)max = 0.007
1312 reflectionsΔρmax = 0.13 e Å3
118 parametersΔρmin = 0.16 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.065 (9)
Crystal data top
C10H8O2V = 752.5 (4) Å3
Mr = 160.16Z = 4
Monoclinic, P21/cMo Kα radiation
a = 9.0606 (18) ŵ = 0.10 mm1
b = 7.2027 (14) ÅT = 293 K
c = 13.309 (3) Å0.50 × 0.30 × 0.05 mm
β = 119.96 (3)°
Data collection top
Oxford Diffraction Xcalibur3 CCD area-detector
diffractometer
1139 reflections with I > 2σ(I)
3650 measured reflectionsRint = 0.025
1312 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0490 restraints
wR(F2) = 0.119H atoms treated by a mixture of independent and constrained refinement
S = 1.17Δρmax = 0.13 e Å3
1312 reflectionsΔρmin = 0.16 e Å3
118 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.2499 (2)0.8877 (3)0.23863 (15)0.0407 (5)
C20.3512 (2)0.8147 (3)0.20084 (16)0.0450 (5)
H20.46900.82110.24710.054*
C30.2778 (2)0.7298 (3)0.09212 (16)0.0415 (5)
C40.1083 (2)0.7167 (3)0.02371 (16)0.0419 (5)
H40.06210.65880.04820.050*
C50.0011 (2)0.7910 (2)0.06155 (15)0.0373 (5)
C60.1773 (2)0.7808 (3)0.00702 (18)0.0474 (5)
H60.22640.72350.07920.057*
C70.2779 (3)0.8535 (3)0.0310 (2)0.0561 (6)
H70.39560.84400.01500.067*
C80.2079 (3)0.9427 (3)0.1382 (2)0.0559 (6)
H80.27900.99330.16280.067*
C90.0369 (3)0.9555 (3)0.20647 (18)0.0477 (5)
H90.00911.01520.27780.057*
C100.0714 (2)0.8792 (2)0.17030 (15)0.0383 (5)
O110.3137 (2)0.9713 (2)0.34456 (12)0.0558 (5)
H110.409 (4)1.020 (5)0.364 (3)0.105 (11)*
O120.38935 (19)0.6626 (2)0.05988 (14)0.0558 (5)
H120.334 (3)0.623 (4)0.014 (2)0.081 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0475 (11)0.0424 (11)0.0311 (10)0.0081 (9)0.0187 (8)0.0006 (8)
C20.0371 (10)0.0573 (13)0.0362 (10)0.0014 (9)0.0151 (9)0.0052 (9)
C30.0440 (11)0.0457 (11)0.0380 (11)0.0062 (9)0.0229 (9)0.0058 (8)
C40.0472 (11)0.0401 (11)0.0360 (10)0.0001 (8)0.0191 (9)0.0006 (8)
C50.0416 (10)0.0318 (10)0.0378 (10)0.0015 (8)0.0193 (8)0.0025 (8)
C60.0433 (11)0.0440 (11)0.0478 (12)0.0017 (9)0.0175 (9)0.0013 (9)
C70.0417 (11)0.0543 (13)0.0715 (16)0.0025 (9)0.0276 (11)0.0080 (11)
C80.0595 (14)0.0517 (13)0.0711 (15)0.0107 (10)0.0436 (12)0.0062 (11)
C90.0618 (13)0.0398 (11)0.0499 (12)0.0039 (9)0.0341 (11)0.0023 (9)
C100.0477 (11)0.0310 (10)0.0406 (11)0.0003 (8)0.0253 (9)0.0045 (8)
O110.0608 (10)0.0700 (11)0.0387 (8)0.0191 (8)0.0264 (7)0.0155 (7)
O120.0473 (8)0.0787 (11)0.0433 (9)0.0153 (7)0.0240 (7)0.0016 (8)
Geometric parameters (Å, º) top
C1—C21.353 (3)C6—C71.350 (3)
C1—O111.368 (2)C6—H60.9300
C1—C101.406 (3)C7—C81.396 (3)
C2—C31.396 (3)C7—H70.9300
C2—H20.9300C8—C91.352 (3)
C3—C41.342 (3)C8—H80.9300
C3—O121.369 (2)C9—C101.403 (3)
C4—C51.404 (3)C9—H90.9300
C4—H40.9300O11—H110.85 (3)
C5—C61.406 (3)O12—H120.89 (3)
C5—C101.408 (3)
C2—C1—O11122.56 (17)C7—C6—H6119.7
C2—C1—C10121.14 (18)C5—C6—H6119.7
O11—C1—C10116.30 (17)C6—C7—C8121.0 (2)
C1—C2—C3119.67 (18)C6—C7—H7119.5
C1—C2—H2120.2C8—C7—H7119.5
C3—C2—H2120.2C9—C8—C7120.10 (19)
C4—C3—O12122.46 (18)C9—C8—H8119.9
C4—C3—C2121.69 (18)C7—C8—H8119.9
O12—C3—C2115.86 (17)C8—C9—C10120.4 (2)
C3—C4—C5119.48 (18)C8—C9—H9119.8
C3—C4—H4120.3C10—C9—H9119.8
C5—C4—H4120.3C9—C10—C1122.48 (18)
C4—C5—C6121.60 (18)C9—C10—C5119.63 (18)
C4—C5—C10120.13 (17)C1—C10—C5117.89 (17)
C6—C5—C10118.28 (18)C1—O11—H11110 (2)
C7—C6—C5120.6 (2)C3—O12—H12110.8 (17)
O11—C1—C2—C3179.44 (17)C7—C8—C9—C100.1 (3)
C10—C1—C2—C30.1 (3)C8—C9—C10—C1179.44 (19)
C1—C2—C3—C40.6 (3)C8—C9—C10—C50.8 (3)
C1—C2—C3—O12178.95 (17)C2—C1—C10—C9179.22 (18)
O12—C3—C4—C5179.12 (17)O11—C1—C10—C91.4 (3)
C2—C3—C4—C50.4 (3)C2—C1—C10—C50.5 (3)
C3—C4—C5—C6179.95 (18)O11—C1—C10—C5178.84 (16)
C3—C4—C5—C100.2 (3)C4—C5—C10—C9179.04 (17)
C4—C5—C6—C7179.89 (19)C6—C5—C10—C90.7 (3)
C10—C5—C6—C70.2 (3)C4—C5—C10—C10.7 (3)
C5—C6—C7—C80.9 (3)C6—C5—C10—C1179.58 (17)
C6—C7—C8—C90.8 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O11—H11···O12i0.84 (4)1.89 (4)2.709 (2)163 (3)
O12—H12···O11ii0.90 (2)1.93 (3)2.766 (2)156 (3)
C9—H9···Cg2iii0.932.903.710 (2)146
Symmetry codes: (i) x+1, y+1/2, z+1/2; (ii) x, y+3/2, z1/2; (iii) x, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC10H8O2
Mr160.16
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)9.0606 (18), 7.2027 (14), 13.309 (3)
β (°) 119.96 (3)
V3)752.5 (4)
Z4
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.50 × 0.30 × 0.05
Data collection
DiffractometerOxford Diffraction Xcalibur3 CCD area-detector
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
3650, 1312, 1139
Rint0.025
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.119, 1.17
No. of reflections1312
No. of parameters118
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.13, 0.16

Computer programs: CrysAlis CCD (Oxford Diffraction, 2002), CrysAlis RED (Oxford Diffraction, 2002), CrysAlis RED, SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003) and RPLUTO (Motherwell et al., 2000), SHELXL97.

Selected geometric parameters (Å, º) top
C1—C21.353 (3)C5—C61.406 (3)
C1—O111.368 (2)C5—C101.408 (3)
C1—C101.406 (3)C6—C71.350 (3)
C2—C31.396 (3)C7—C81.396 (3)
C3—C41.342 (3)C8—C91.352 (3)
C3—O121.369 (2)C9—C101.403 (3)
C4—C51.404 (3)
C2—C1—O11122.56 (17)C4—C5—C10120.13 (17)
C2—C1—C10121.14 (18)C6—C5—C10118.28 (18)
O11—C1—C10116.30 (17)C7—C6—C5120.6 (2)
C1—C2—C3119.67 (18)C6—C7—C8121.0 (2)
C4—C3—O12122.46 (18)C9—C8—C7120.10 (19)
C4—C3—C2121.69 (18)C8—C9—C10120.4 (2)
O12—C3—C2115.86 (17)C9—C10—C1122.48 (18)
C3—C4—C5119.48 (18)C1—C10—C5117.89 (17)
C4—C5—C6121.60 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O11—H11···O12i0.84 (4)1.89 (4)2.709 (2)163 (3)
O12—H12···O11ii0.90 (2)1.93 (3)2.766 (2)156 (3)
C9—H9···Cg2iii0.932.903.710 (2)146
Symmetry codes: (i) x+1, y+1/2, z+1/2; (ii) x, y+3/2, z1/2; (iii) x, y+1/2, z+1/2.
 

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